HU189166B - Process for producing pyridazin-amine derivatives - Google Patents
Process for producing pyridazin-amine derivatives Download PDFInfo
- Publication number
- HU189166B HU189166B HU822542A HU254282A HU189166B HU 189166 B HU189166 B HU 189166B HU 822542 A HU822542 A HU 822542A HU 254282 A HU254282 A HU 254282A HU 189166 B HU189166 B HU 189166B
- Authority
- HU
- Hungary
- Prior art keywords
- formula
- compounds
- amine
- hydrogen
- reaction
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 14
- LETVJWLLIMJADE-UHFFFAOYSA-N pyridazin-3-amine Chemical class NC1=CC=CN=N1 LETVJWLLIMJADE-UHFFFAOYSA-N 0.000 title claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 30
- 239000002253 acid Substances 0.000 claims description 13
- 238000006243 chemical reaction Methods 0.000 claims description 9
- 150000003839 salts Chemical class 0.000 claims description 9
- 150000001412 amines Chemical class 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 239000008194 pharmaceutical composition Substances 0.000 claims description 7
- 239000002904 solvent Substances 0.000 claims description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- IBWYHNOFSKJKKY-UHFFFAOYSA-N 3-chloropyridazine Chemical class ClC1=CC=CN=N1 IBWYHNOFSKJKKY-UHFFFAOYSA-N 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 125000005036 alkoxyphenyl group Chemical group 0.000 claims description 3
- 125000004464 hydroxyphenyl group Chemical group 0.000 claims description 3
- 238000010992 reflux Methods 0.000 claims description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 230000002378 acidificating effect Effects 0.000 claims 1
- 239000003054 catalyst Substances 0.000 claims 1
- 229910052802 copper Inorganic materials 0.000 claims 1
- 239000010949 copper Substances 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 230000000694 effects Effects 0.000 description 14
- 238000012360 testing method Methods 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 241001465754 Metazoa Species 0.000 description 7
- 230000001773 anti-convulsant effect Effects 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 241000699670 Mus sp. Species 0.000 description 5
- 239000001961 anticonvulsive agent Substances 0.000 description 5
- 229960003965 antiepileptics Drugs 0.000 description 5
- LDMWSLGGVTVJPG-UHFFFAOYSA-N minaprine Chemical compound CC1=CC(C=2C=CC=CC=2)=NN=C1NCCN1CCOCC1 LDMWSLGGVTVJPG-UHFFFAOYSA-N 0.000 description 5
- 229960004758 minaprine Drugs 0.000 description 5
- DNXIKVLOVZVMQF-UHFFFAOYSA-N (3beta,16beta,17alpha,18beta,20alpha)-17-hydroxy-11-methoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-yohimban-16-carboxylic acid, methyl ester Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(C(=O)OC)C(O)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 DNXIKVLOVZVMQF-UHFFFAOYSA-N 0.000 description 4
- 206010015995 Eyelid ptosis Diseases 0.000 description 4
- LCQMZZCPPSWADO-UHFFFAOYSA-N Reserpilin Natural products COC(=O)C1COCC2CN3CCc4c([nH]c5cc(OC)c(OC)cc45)C3CC12 LCQMZZCPPSWADO-UHFFFAOYSA-N 0.000 description 4
- QEVHRUUCFGRFIF-SFWBKIHZSA-N Reserpine Natural products O=C(OC)[C@@H]1[C@H](OC)[C@H](OC(=O)c2cc(OC)c(OC)c(OC)c2)C[C@H]2[C@@H]1C[C@H]1N(C2)CCc2c3c([nH]c12)cc(OC)cc3 QEVHRUUCFGRFIF-SFWBKIHZSA-N 0.000 description 4
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 4
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 201000003004 ptosis Diseases 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- BJOIZNZVOZKDIG-MDEJGZGSSA-N reserpine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C([C]5C=CC(OC)=CC5=N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 BJOIZNZVOZKDIG-MDEJGZGSSA-N 0.000 description 4
- 229960003147 reserpine Drugs 0.000 description 4
- MDMGHDFNKNZPAU-UHFFFAOYSA-N roserpine Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(OC(C)=O)C(OC)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 MDMGHDFNKNZPAU-UHFFFAOYSA-N 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 230000001430 anti-depressive effect Effects 0.000 description 3
- 239000000935 antidepressant agent Substances 0.000 description 3
- 229940005513 antidepressants Drugs 0.000 description 3
- 238000003556 assay Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- CTKLICXVGAUHHC-UHFFFAOYSA-N n'-(4-methyl-6-phenylpyridazin-3-yl)ethane-1,2-diamine;dihydrochloride Chemical compound Cl.Cl.N1=C(NCCN)C(C)=CC(C=2C=CC=CC=2)=N1 CTKLICXVGAUHHC-UHFFFAOYSA-N 0.000 description 3
- 230000000144 pharmacologic effect Effects 0.000 description 3
- SSOLNOMRVKKSON-UHFFFAOYSA-N proguanil Chemical class CC(C)\N=C(/N)N=C(N)NC1=CC=C(Cl)C=C1 SSOLNOMRVKKSON-UHFFFAOYSA-N 0.000 description 3
- 230000001988 toxicity Effects 0.000 description 3
- 231100000419 toxicity Toxicity 0.000 description 3
- AAILEWXSEQLMNI-UHFFFAOYSA-N 1h-pyridazin-6-one Chemical class OC1=CC=CN=N1 AAILEWXSEQLMNI-UHFFFAOYSA-N 0.000 description 2
- ROVPWRBPJHXFRE-UHFFFAOYSA-N 3-chloro-4-methyl-6-phenylpyridazine Chemical compound N1=C(Cl)C(C)=CC(C=2C=CC=CC=2)=N1 ROVPWRBPJHXFRE-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 210000003169 central nervous system Anatomy 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- ZUDCSNNVEXBABY-UHFFFAOYSA-N n',n'-dimethyl-n-(4-methyl-6-phenylpyridazin-3-yl)ethane-1,2-diamine;dihydrochloride Chemical compound Cl.Cl.C1=C(C)C(NCCN(C)C)=NN=C1C1=CC=CC=C1 ZUDCSNNVEXBABY-UHFFFAOYSA-N 0.000 description 2
- PMHUBFCZZSUJPT-UHFFFAOYSA-N n'-(4-phenylpyridazin-3-yl)ethane-1,2-diamine;dihydrochloride Chemical compound Cl.Cl.NCCNC1=NN=CC=C1C1=CC=CC=C1 PMHUBFCZZSUJPT-UHFFFAOYSA-N 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 2
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- -1 2-Aminoethylamino Chemical group 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- XQMSOYJVSMNXSV-UHFFFAOYSA-N 3-chloro-6-(4-methoxyphenyl)-4-methylpyridazine Chemical compound C1=CC(OC)=CC=C1C1=CC(C)=C(Cl)N=N1 XQMSOYJVSMNXSV-UHFFFAOYSA-N 0.000 description 1
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 1
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229910002012 Aerosil® Inorganic materials 0.000 description 1
- LHBIYVKJPZQBQY-UHFFFAOYSA-N Cl.NCCNC=1N=NC(=CC1C)C1=CC=CC=C1 Chemical compound Cl.NCCNC=1N=NC(=CC1C)C1=CC=CC=C1 LHBIYVKJPZQBQY-UHFFFAOYSA-N 0.000 description 1
- 208000026139 Memory disease Diseases 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- 208000029808 Psychomotor disease Diseases 0.000 description 1
- 239000005700 Putrescine Substances 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 230000008485 antagonism Effects 0.000 description 1
- 230000003276 anti-hypertensive effect Effects 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 230000002526 effect on cardiovascular system Effects 0.000 description 1
- PSLIMVZEAPALCD-UHFFFAOYSA-N ethanol;ethoxyethane Chemical compound CCO.CCOCC PSLIMVZEAPALCD-UHFFFAOYSA-N 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- QYRFJLLXPINATB-UHFFFAOYSA-N hydron;2,4,5,6-tetrafluorobenzene-1,3-diamine;dichloride Chemical class Cl.Cl.NC1=C(F)C(N)=C(F)C(F)=C1F QYRFJLLXPINATB-UHFFFAOYSA-N 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 231100001231 less toxic Toxicity 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 208000024714 major depressive disease Diseases 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- GQSOZJPUDBYTHB-UHFFFAOYSA-N n',n'-diethyl-n-(4-methyl-6-phenylpyridazin-3-yl)ethane-1,2-diamine;oxalic acid Chemical compound OC(=O)C(O)=O.OC(=O)C(O)=O.C1=C(C)C(NCCN(CC)CC)=NN=C1C1=CC=CC=C1 GQSOZJPUDBYTHB-UHFFFAOYSA-N 0.000 description 1
- IHGHYTVLKPZYEV-UHFFFAOYSA-N n'-(4-methyl-6-phenylpyridazin-3-yl)butane-1,4-diamine Chemical compound N1=C(NCCCCN)C(C)=CC(C=2C=CC=CC=2)=N1 IHGHYTVLKPZYEV-UHFFFAOYSA-N 0.000 description 1
- YUNISNGIGFBFJU-UHFFFAOYSA-N n'-(4-methyl-6-phenylpyridazin-3-yl)butane-1,4-diamine;dihydrochloride Chemical compound Cl.Cl.N1=C(NCCCCN)C(C)=CC(C=2C=CC=CC=2)=N1 YUNISNGIGFBFJU-UHFFFAOYSA-N 0.000 description 1
- VIUDAFUCYIXLKN-UHFFFAOYSA-N n'-(4-methyl-6-phenylpyridazin-3-yl)propane-1,3-diamine Chemical compound N1=C(NCCCN)C(C)=CC(C=2C=CC=CC=2)=N1 VIUDAFUCYIXLKN-UHFFFAOYSA-N 0.000 description 1
- YKRYWHZLNMDTRV-UHFFFAOYSA-N n'-(4-methyl-6-phenylpyridazin-3-yl)propane-1,3-diamine;dihydrochloride Chemical compound Cl.Cl.N1=C(NCCCN)C(C)=CC(C=2C=CC=CC=2)=N1 YKRYWHZLNMDTRV-UHFFFAOYSA-N 0.000 description 1
- KALMSEOPWTVCIF-UHFFFAOYSA-N n'-(6-phenylpyridazin-3-yl)ethane-1,2-diamine;dihydrochloride Chemical compound Cl.Cl.N1=NC(NCCN)=CC=C1C1=CC=CC=C1 KALMSEOPWTVCIF-UHFFFAOYSA-N 0.000 description 1
- HRTLDHYWCFITKP-UHFFFAOYSA-N n'-[6-(4-methoxyphenyl)-4-methyl-1h-pyridazin-2-yl]ethane-1,2-diamine Chemical compound C1=CC(OC)=CC=C1C1=CC(C)=CN(NCCN)N1 HRTLDHYWCFITKP-UHFFFAOYSA-N 0.000 description 1
- KFIGICHILYTCJF-UHFFFAOYSA-N n'-methylethane-1,2-diamine Chemical compound CNCCN KFIGICHILYTCJF-UHFFFAOYSA-N 0.000 description 1
- FAXNSIHPVPBXIA-UHFFFAOYSA-N n-methyl-n'-(4-methyl-6-phenylpyridazin-3-yl)ethane-1,2-diamine Chemical compound C1=C(C)C(NCCNC)=NN=C1C1=CC=CC=C1 FAXNSIHPVPBXIA-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000002385 psychotomimetic effect Effects 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- 150000004892 pyridazines Chemical class 0.000 description 1
- 239000002516 radical scavenger Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 230000000304 vasodilatating effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
- C07D237/02—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings
- C07D237/06—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D237/10—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D237/20—Nitrogen atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/26—Psychostimulants, e.g. nicotine, cocaine
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Psychiatry (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Biomedical Technology (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pain & Pain Management (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8115380A FR2510998B1 (fr) | 1981-08-07 | 1981-08-07 | Nouveaux derives amines de la pyridazine, leur procede de preparation et les medicaments, a action desinhibitrice, qui en comportent |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HU189166B true HU189166B (en) | 1986-06-30 |
Family
ID=9261294
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU822542A HU189166B (en) | 1981-08-07 | 1982-08-06 | Process for producing pyridazin-amine derivatives |
| HU822545A HU190028B (en) | 1981-08-07 | 1982-08-06 | Process for preparing pyridazine derivatives |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU822545A HU190028B (en) | 1981-08-07 | 1982-08-06 | Process for preparing pyridazine derivatives |
Country Status (30)
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2540113A1 (fr) * | 1983-01-27 | 1984-08-03 | Sanofi Sa | Acides derives de la pyridazine actifs sur le systeme nerveux central |
| CA1218655A (en) * | 1983-01-28 | 1987-03-03 | Kathleen Biziere | Process for the preparation of pyridazine derivatives having a psychotropic action |
| US4628088A (en) * | 1984-07-17 | 1986-12-09 | Eli Lilly And Company | Preparation of substituted pyridazines |
| DE3664772D1 (en) * | 1985-01-14 | 1989-09-07 | Boehringer Ingelheim Kg | 12-amino pyridazinoû4',5':3,4¨pyrroloû2,1-a¨isoquinolines, process for their preparation and use |
| PT93060B (pt) | 1989-02-07 | 1995-12-29 | Sanofi Sa | Processo para a obtencao de derivados de piridazina e de composicoes farmaceuticas que os contem |
| FR2642754B1 (fr) * | 1989-02-07 | 1991-05-24 | Sanofi Sa | Nouveaux derives de la pyridazine, procede de preparation et compositions pharmaceutiques en contenant |
| FR2665442B1 (fr) * | 1990-07-31 | 1992-12-04 | Sanofi Sa | Derives d'alkyl-6 pyridazine, procede de preparation et compositions pharmaceutiques en contenant. |
| US5631255A (en) * | 1989-02-07 | 1997-05-20 | Sanofi | Pyridazine derivatives |
| FR2642648B1 (fr) * | 1989-02-07 | 1991-06-21 | Sanofi Sa | Utilisation de derives d'alkyl-5 pyridazine comme medicaments actifs sur le systeme cholinergique |
| FR2654727B1 (fr) * | 1989-11-17 | 1992-03-27 | Sanofi Sa | Derives de la pyridazine, procede de preparation et compositions pharmaceutiques en contenant. |
| US5461053A (en) * | 1989-02-07 | 1995-10-24 | Sanofi | Pyridazine derivatives |
| FR2663326B2 (fr) * | 1989-11-17 | 1992-10-16 | Sanofi Sa | Derives de la pyridazine, procede de preparation et compositions pharmaceutiques en contenant. |
| FR2676444B1 (fr) * | 1991-05-16 | 1995-03-10 | Sanofi Elf | Nouveaux derives d'amino-3 pyridazines actifs sur le systeme nerveux central, procede de preparation et compositions pharmaceutiques en contenant. |
| US20100210590A1 (en) * | 1995-09-27 | 2010-08-19 | Northwestern University | Compositions and treatments for seizure-related disorders |
| EP1430033A4 (en) * | 2001-08-31 | 2004-12-15 | Univ Northwestern | ANTI-INFLAMMATORY AND PROTEIN-INK-INHIBITING COMPOSITION AND THEIR USE |
| JP2006507237A (ja) * | 2002-08-13 | 2006-03-02 | メルク シャープ エンド ドーム リミテッド | Ｇａｂａ受容体に対するリガンドとしてのフェニルピリダジン誘導体 |
| JP5337375B2 (ja) | 2004-11-02 | 2013-11-06 | ノースウェスタン ユニバーシティ | ピリダジン化合物、組成物および方法 |
| JP2008518955A (ja) * | 2004-11-02 | 2008-06-05 | ノースウェスタン ユニバーシティ | ピリダジン化合物および方法 |
| WO2007127474A2 (en) * | 2006-04-28 | 2007-11-08 | Northwestern University | Compositions and treatments using pyridazine compounds and cholinesterase inhibitors |
| WO2007127448A2 (en) * | 2006-04-28 | 2007-11-08 | Northwestern University | Salts of pyridazine compounds |
| CN101754762A (zh) * | 2006-04-28 | 2010-06-23 | 西北大学 | 用于治疗神经炎症性疾病的包含哒嗪化合物的制剂 |
| RU2555969C1 (ru) * | 2014-07-09 | 2015-07-10 | Юлия Алексеевна Щепочкина | Керамическая масса для изготовления облицовочной плитки |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1345880A (en) * | 1971-06-18 | 1974-02-06 | Cepbepe | Pyridazine derivatives |
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1981
- 1981-08-07 FR FR8115380A patent/FR2510998B1/fr not_active Expired
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1982
- 1982-07-21 NO NO822509A patent/NO157861C/no unknown
- 1982-07-21 NO NO822510A patent/NO157102C/no unknown
- 1982-07-23 IE IE1778/82A patent/IE53387B1/en not_active IP Right Cessation
- 1982-07-23 IE IE1779/82A patent/IE53388B1/en not_active IP Right Cessation
- 1982-07-26 GR GR68873A patent/GR76430B/el unknown
- 1982-07-26 GR GR68868A patent/GR76429B/el unknown
- 1982-07-27 IL IL66408A patent/IL66408A/xx unknown
- 1982-07-27 IL IL66409A patent/IL66409A/xx unknown
- 1982-07-29 AU AU86554/82A patent/AU548931B2/en not_active Ceased
- 1982-07-29 AU AU86553/82A patent/AU548930B2/en not_active Ceased
- 1982-07-29 US US06/402,906 patent/US4508720A/en not_active Expired - Fee Related
- 1982-07-30 EP EP82401424A patent/EP0074863B1/fr not_active Expired
- 1982-07-30 ZA ZA825512A patent/ZA825512B/xx unknown
- 1982-07-30 DE DE8282401424T patent/DE3269383D1/de not_active Expired
- 1982-07-30 ZA ZA825513A patent/ZA825513B/xx unknown
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- 1982-07-30 AT AT82401425T patent/ATE12227T1/de not_active IP Right Cessation
- 1982-07-30 DE DE8282401425T patent/DE3262671D1/de not_active Expired
- 1982-07-30 PT PT75351A patent/PT75351B/pt not_active IP Right Cessation
- 1982-07-30 AT AT82401424T patent/ATE18216T1/de not_active IP Right Cessation
- 1982-07-30 EP EP82401425A patent/EP0072726B1/fr not_active Expired
- 1982-08-02 MA MA19771A patent/MA19560A1/fr unknown
- 1982-08-02 MA MA19773A patent/MA19562A1/fr unknown
- 1982-08-03 CS CS825800A patent/CS229941B2/cs unknown
- 1982-08-03 CS CS825799A patent/CS229940B2/cs unknown
- 1982-08-04 EG EG473/82A patent/EG15788A/xx active
- 1982-08-04 EG EG82474A patent/EG15747A/xx active
- 1982-08-06 SU SU823475704A patent/SU1138024A3/ru active
- 1982-08-06 JP JP57137832A patent/JPS5877867A/ja active Granted
- 1982-08-06 PH PH27679A patent/PH18545A/en unknown
- 1982-08-06 CA CA000408843A patent/CA1174240A/en not_active Expired
- 1982-08-06 AR AR290242A patent/AR231441A1/es active
- 1982-08-06 PL PL1982237808A patent/PL137199B1/pl unknown
- 1982-08-06 FI FI822748A patent/FI72969C/fi not_active IP Right Cessation
- 1982-08-06 OA OA57768A patent/OA07176A/xx unknown
- 1982-08-06 PL PL1982237809A patent/PL130647B1/pl unknown
- 1982-08-06 OA OA57767A patent/OA07175A/xx unknown
- 1982-08-06 FI FI822747A patent/FI72968C/fi not_active IP Right Cessation
- 1982-08-06 DK DK354382A patent/DK148537C/da not_active IP Right Cessation
- 1982-08-06 HU HU822542A patent/HU189166B/hu not_active IP Right Cessation
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- 1982-08-06 NZ NZ201520A patent/NZ201520A/xx unknown
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- 1982-08-06 ES ES514795A patent/ES514795A0/es active Granted
- 1982-08-06 YU YU01718/82A patent/YU171882A/xx unknown
- 1982-08-06 CA CA000408844A patent/CA1179346A/en not_active Expired
- 1982-08-06 SU SU823476698A patent/SU1140685A3/ru active
- 1982-08-06 JP JP57137833A patent/JPS5877868A/ja active Pending
- 1982-08-06 ES ES514794A patent/ES8305737A1/es not_active Expired
- 1982-08-06 AR AR290243A patent/AR231637A1/es active
- 1982-08-06 NZ NZ201518A patent/NZ201518A/en unknown
- 1982-08-06 HU HU822545A patent/HU190028B/hu not_active IP Right Cessation
- 1982-08-07 KR KR8203557A patent/KR890001569B1/ko not_active Expired
- 1982-08-07 KR KR8203558A patent/KR880001624B1/ko not_active Expired
- 1982-08-09 DD DD82242359A patent/DD202549A5/de unknown
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| HU90 | Patent valid on 900628 | ||
| HMM4 | Cancellation of final prot. due to non-payment of fee |